Cheer Up, Lindsey
by Exotos135
Summary: By request of a certain redhead, Chandler is put in charge of walking back Lindsey Sweetwater home, and make sure she's happy when she returns.


At the auditorium of the Royal Woods, the most recent beauty pageant had just finished, with Lola obviously landing in first place. However, a much more interesting sight came from Chandler, who leaned his back against the wall close to the exit as he waited for the award ceremony to end.

"Ugh, this is ridiculous," Chandler complained, shaking his head in annoyance. "Why did I agree to do this?"

Just as he started to question that, the boy suddenly remembered the events that brought him here.

 _Chandler's flashback..._

The boy leaned against the wall at the back of the school, while a familiar girl, Cristina looked at him with her hands on her hips.

"So, what's the reason you called me out here?" Chandler asked as he put his hands on his pockets. "I'll let you know that I'm very popular and got tons of followers, so if this is some sort of prank-"

"I need you to cheer up my sister," Cristina suddenly stated, with quite the deep voice for an 11 year old.

"E-Excuse me?" Chandler asked, flinching at the sudden talk.

"Okay, let's start with the simple information," Cristina folded her arms. "My name's Cristina Sweetwater, and I have a younger sister named Lindsey Sweetwater. She's a fan of beauty pageants, and she has a rivalry with an infamous participant of those things, Lola Loud. Do you follow?"

Chandler quickly wrote down all the info Cristina gave her on a notepad, then turned back to the redhead and nodded, prompting her to continue:

"Every single time they face off, Lola always end up in first place, with Lindsey commonly landing in second place. That has brought down her morale recently, and while I would cheer her up myself, I'm kinda busy today, so I need somebody else to do it for me."

Cristina took out 40 bucks and handed them to Chandler as she finished:

"From what I heard, you're popular with the girls, so if you can please several girls your age, pleasing a six year old should be no issue, right?"

The boy eyed the money he was given, and thought about his answer...

 _Back in the present..._

"Right..." the boy couldn't help but shake his head in annoyance. "Well, let's hope this little brat doesn't have mascara running down her cheeks or something. That'd just make this feel even worse than it already does."

And then, Lindsey herself came out once everything was said and done. She was wearing a green pageant gown, lime green opera gloves, and for some reason, crimson wavvy hair.

She also had blue eyes, which caught Chandler's attention. After all, a redheaded girl, who didn't have green eyes? What kind of madness was this?!

And then Lindsey noticed him and asked, "Who are you, mister...?"

"Chandler, my name's Chandler," the boy quickly answered. "I was asked by your sister to take you on a walk back to your house."

Lindsey tilted her head, having no idea who Chandler was talking about. Either that, or she didn't know whether to trust the redhead's word or not. And so, he further explained:

"She's a redhead, wears an orange headband..."

Chandler promptly got on a pose that implied surprise.

"She's seen in this pose most of the time, and she also has her mouth like this."

The boy opened his mouth to imply a gasp, and an actual gasp came from Lindsey, who chirped, "That's Cristina!"

Chandler stopped doing the pose and put his hands on his hips. "Yeah, her, she asked me to take you on a walk back home, and cheer you up too while we're at it."

"But it's usually her job to do that, and she never lets anybody else do it unless it's an emergency," Lindsey remarked, tilting her head again. "Why did she have you do it intstead?"

"You know, that's exactly what I asked her," the freckled redhead put his hands on his pockets. "And you know what she told me? That she had to deal with a client."

 _Meanwhile, with Cristina..._

Cristina, wearing glasses and holding a clipboard, sat on a chair as Lori Loud sat on a couch next to her.

"So," Cristina put her pen and clipboard down and raised an eyebrow. "How about we start with the beginning?"

Lori took a deep breath and started, "Well, it all literally started when I got my first phone..."

 _Back at the obviously more interesting main plot..._

"Oh right, she did say she had to help a patient today," Lindsey sighed and shook her head. "She's going to be there for a while, she's one of the best and most determined phone therapists I know."

"I still can't believe phone therapist's an actual thing," Chandler put his hands on his pockets. "Anyway, she also told me to cheer you up on the way there, so, what would bring up your spirits right now?"

"Defeat Lola once and for all!" Lindsey chirped, lifting a fist.

"I don't think I can do that right now, sorry," Chandler remarked. "Anything else?"

"Hmm... Ice cream always manages to put a smile on my face," Lindsey clasped her hands. "Do you think you could buy me one?"

The boy checked his pocket, and took out the 40 bucks, which he and the girl glanced at as he said:

"Your sister gave me this money in order to be able to buy whatever could be able to cheer you up. Perhaps we could go buy one of those treats nearby?"

Lindsey nodded and immediately grabbed Chandler's arm with her hands. And strangely enough, the boy seemed... Kinda uncomfortable with this gesture.

"What are you doing?" he asked, raising an eyebrow.

"I'm grabbing your arm so we don't get separated on the walk home," Lindsey answered with a smile. "Is there something wrong with that?"

"N-No, I'm just not used to girls doing that to me," Chandler looked away and scratched the back of his head. "Come to think of it, I'm not used to hanging out with a girl in the first place. Specially not one as young as you."

The instant he saw Lindsey look at the ground with a sad look, he quickly corrected himself:

"B-B-But it's okay, I don't mind it this time! As long as you're happy, I'm happy too... Let's just go get some ice cream, okay?"

The girl immediately cheered up and nodded with a blush. And so, the pair walked out of the school, all while Chandler couldn't help but notice people looking at them with surprise and shock. Mostly shock.

" _Now I really hope this walk back home better be worth it,_ " Chandler thought in exasperation. " _If the only thing I gain from doing this request is people teasing me about this girl and our non-existant relationship, I'm definitely going to speak my mind to that Cristina._ "

"We're here!" Lindsey chirped.

The redheaded pair stopped and turned around to see the ice cream shop, which Lindsey dragged Chandler into almost immediately. And much to their surprise-and relief-the shop wasn't all that full, so getting the ice cream should be a piece of ice cream cake.

"Alright, this should be pretty quick," Chandler stated with confidence. "Lindsey, how about you go wait at the tables while I buy the ice cream."

The redhead beamed a smile. "Got it, Chandelier!"

The boy couldn't help but flinch. "What did you call me?"

"Chandelier. You know, as a cute little nickname!"

"Well, please don't call me that, it makes it sound like I'm an object to you," the boy requested, trying not to sound too hard on the girl. "Why even give me a nickname, anyway?"

"'Cause I like you!" Lindsey cooed. "I really do!"

Though caught off-guard by the redhead's rather straightforward answer, he still felt rather flattered and pleased by it. After all, it wasn't often that he heard somebody tell him "I like you" without being forced or bribed into doing so.

Then, without even being reminded to do so, Lindsey strolled to the tables, but not before loudly shouting to Chandler: "Oh, and I want a four-ball ice cream, one chocolate, one vanilla, one strawberry, and one lemon, got it?"

Chandler pulled a thumbs up, and the person right next in line to him, a certain blonde named Paige, took the chance to say, "Aw, is she your younger sister?"

"Well, she's someone's younger sister, but not mine," Chandler quickly corrected. "I'm making sure she comes back home happy by their request, that's all."

"That's oddly nice of you," Paige narrowed her eyes and gasped. "Oh wait, I think I can recognize you... You're Chandler, the boy who had his birthday party on a sewage plant, right?"

The redhead folded his arms. "I'm not someone who likes to boast, but just this once, I'll say that I'm the guy you're talking about!"

"I feel sorry for you," Paige suddenly said. "I mean, a sewage plant is probably one of the worst places to have a birthday party, wouldn't you agree?"

Any happiness or pride Chandler felt in that moment faded away, as the boy looked at the ground and nervously answered:

"I... I guess so..."

All while Lindsey watched nearby.

Not that this mattered a whole lot, since Chandler eventually managed to buy Lindsey's rather large ice cream, which he handed her as he sat next to her, for company purposes.

"Here you go, a four ball chocolate-vanilla-strawberry-lemon ice cream," the redhead guy said, with Lindsey eyeing her ice cream as he quipped, "Try to say that three times fast."

However, Lindsey didn't answer. In fact, she didn't even move at all, she just watched her ice cream with an upset look, even as it obviously started to melt.

"Lindsey?" Chandler asked, returning the pageant participant's attention. "Is something on your mind? You're just letting your ice cream melt while looking at it."

"Nothing's wrong, I'm just curious: where's your ice cream, Chandler?" Lindsey inquired, tilting her head to the left.

"I decided to only use some of the money to buy you your ice cream," Chandler nonchalantly explained. "That way, if we find something else that could cheer you up, we have some money for it so we can do it."

"But that isn't fair, you deserve some ice cream too..." Lindsey got an idea. "I know! Let's share some of mine! You don't mind a chocolate-vanilla-strawberry-lemon flavor, do you?"

 _"First she asks for a four-ball ice cream, and now she wants to share some of it with me? This girl really is weird,_ " Chandler shook his head. "No, I don't mind it. As long as you're happy, I'm happy."

Lindsey leaned her ice cream cone closer to Chandler, though not close enough so one of the flavor balls would fall off. The guy looked to his left and right, then took a big bite of the top ball, the chocolate one. And as he moaned in delight at the taste, Lindsey blushed and smiled, which caused the guy to look away and swallow the ball in embarrassment.

And as his ensuing brain freeze proved, that was a terrible idea.

"Oh goodness, Chandler, are you okay?!" Lindsey exclaimed.

"Yeah, I'm alright," the boy groaned, grabbing his head. "Just a simple brain freeze, getting close to something hot will likely help me-"

Suddenly, Lindsey grabbed Chandler's head and pulled him right into her chest, hugging him tightly as the guy finished with confusion:

"-Deal with it?"

And after a couple seconds, when the boy felt much better, Lindsey released him and clasped her hands as she asked, "Are you feeling better now?"

"Yeah," the boy nodded. "Let's try eating the ice cream a bit more slowly now."

"Are you talking in the plural sense?" Lindsey giggled.

Chandler flinched and looked away, "I mean, next time you offer me some ice cream, I'll eat it slowly."

The redhead leaned her ice cream closer to the boy, and seeing this as a gesture that she wanted to share, the redheads licked the sweet slowly, blushing a little as their gazes met: Chandler looking like he felt awkward by what was going on, while Lindsey was delighted.

And once that was over with, the redheads continued their walk back home, with Lindsey once again grabbing Chandler's arm.

"So, did you like the ice cream?" Chandler inquired, putting up a smile.

Lindsey just nodded before saying, "It was pretty sweet!"

"Well, duh, it was ice cream," Chandler rolled his eyes. "Sure, the lemon flavor was a bit sour, but what can you do when you deal with lemons?"

"That's not what I meant, silly!" Lindsey giggled. "I mean, what you did for me, buying the ice cream and stuff. That was sweet."

The boy sighed. "Well, Lindsey, I'm supposed to bring you back to your house in a cheerful state, and if all I need to do to achieve that is buy you some ice cream-"

"Oh my gosh, is that the county fair?!"

Chandler opened his eyes and turned around to see the duo were at the entrance to the Royal Woods county fair, with Lindsey's eyes glowing with sheer delight at the possibility of visiting the fair, while Chandler looked on deadpanly.

"Oh, right, I forgot that the county fair was happening tod-" Chandler said, dragging on the "a" as Lindsey dragged him deeper inside the fair.

And once they had entered the fair, Chandler was caught off-guard by the amount of games and attractions available: Cotton candy, popcorn, a movie theater, a rollercoaster-come to think of it, did they go to the county fair or a freaking amusement park?

It's not like the redheaded guy hadn't been to a county fair before, but they were never this... Extravagant.

"Oh, look at that!" Lindsey exclaimed, her eyes turning into stars as she clasped her hands. "It's so cute!"

The boy turned around and saw the thing the girl was pointing at: Basically a giant teddy bear, but this one was unlike any other teddy bear in the prize corner, since it was red rather than brown.

"Can you win that teddy bear for me, Chandler?!" Lindsey blurted, catching the freckled redhead's attention.

The boy sighed, "Would you be happy if I did that?"

Lindsey nodded with excitement as her eyes glew with utter joy.

Chandler blushed and quickly turned back to the game as he proclaimed:

"Alright, let's get you a teddy bear!"

So the redheaded duo walked forth to the ball-throwing game, and the guy stopped at the counter and scanned the game.

It seemed like a fairly simple game: Throw the ball, make all the bottles fall, and then you win a prize, in this case the teddy bear. However, being a petty freeloader at times, Chandler knew the basic trick to this kind of games: have the bottles glued, or the balls not optimal for throwing, or otherwise.

However, he couldn't tell if what sort of trick this game had in particular.

"Chandler?" Lindsey inquired, breaking the freckled freeloader's concentration. "I don't wanna sound impatient, but you need to get me that teddy bear quickly so we don't reach my house late."

"Oh, r-right," the boy grabbed a ball and got ready to thrown. "Wish me luck."

Chandler prepared to throw the ball as if he was in

And they all fell down in one clean swoop.

The boy just stood there in disbelief as Lindsey cheerfully received the giant red teddy bear, and hugged it with absolute delight. However, her joy wasn't his main focus right now, rather, it was the fact that the game was genuinely playable, rather than rigged in anyway.

"Chandler, let's keep going!"

The guy returned to reality and turned around to face Lindsey, who grabbed his arm with her hand while she used her free arm to hold her teddy bear.

"Uh sure," Chandler answered. "But that bear seems to be a bit heavy, how about I carry it until we get home?"

"Well, if you insist!"

Lindsey handed Chandler the giant crimson teddy bear, and so he carried it all the way back to Lindsey's house... Which was a two-floor building, rather modest for someone who looked like some sort of discount princess.

And of course, the person who answered the door just had to be Cristina.

"Hi, Cristina," Chandler greeted as he handed Lindsey her teddy bear back.

"Hi, Chandler," the redheaded girl answered sternly, before putting on a cheerful tone with her sister. "Hi, Lindsey. So, how did everything go?"

"Amazing!" the pageant participant chirped. "First we went to get ice cream, and then we went to the fair, and Chandler won me this giant teddy bear! He told me at the beginning that you sent him to cheer me up after my defeat, and I'm so glad you did! He's an awesome guy!"

The boy blushed at being given such glowing praise from the girl, but that blush soon vanished as Lindsey went inside and he was left alone to face Cristina, who leaned against the door frame and folded her arms with a deadpan frown.

"I'm gonna be honest with you: I thought you were going to fail to cheer up Lindsey," Cristina bluntly stated, causing the freckled redhead to look away. "Specially since there are very few things that can cheer her up after a defeat in a beauty pageant."

The boy looked away, having shared the sentiment from the beginning.

"But, I'll admit, you impressed me," Cristina smiled. "Thanks for making sure my sister came back home happy. I'm sure she's going to remember this for a long while. And of course, I also have a little prize for you."

Just as Chandler pondered what that could be, Cristina grabbed him by the neck of his shirt, pulled him forward, and planted a kiss on his lips. She kept the kiss for a couple seconds before separating from the guy, and whispering, with flirty tone:

"Keep this between us, alright? See ya."

Cristina let Chandler go, and closed the door, with the sound of the door being slammed shut returning Chandler back to reality. He took a deep breath, put his hands on his pockets, and turned around and walked back to his house.

And inside the Sweetwater residence, Cristina went up to her younger sister's bedroom to check up on her, make sure she was doing okay.

"Hey, Lindsey, do you-"

However, Cristina stopped right then and there when she saw something she very rarely saw: Lindsey was playing with her giant teddy bear, rather than trying to make new strategies to defeat and dethrone Lola once and for all.

"I'm going to call you, Chandler Junior," Lindsey said before hugging the teddy bear. "And I'm going to love you forever!"

Pleased by this sight, Cristina smiled and closed the door, satisfied with her sister's happiness.

Speaking of satisfaction, as Chandler walked back home with the sunset in the horizon, the boy clutched his chest as he felt... Satisfied, though he couldn't quite understand why. After all, the only thing he did was give that Lindsey girl a walk home, right?

Sure, he may've brought her ice cream...

And taken her to the county fair...

And won that stupidly large teddy bear for her...

But that was all necessary to bring up her spirits once more.

And yet, he still felt... Satisfied from doing all that.

And he apparently thought about that for a while, since by the time he returned to reality, he was standing outside the door to his house, with his cousin Becky calling him to come inside.

"Oh, sorry Becky, I was..." Chandler briefly looked at the ground, then turned back to his cousin. "Lost in thought."

"You? Lost in thought? Now that's something I don't see everyday," Becky quipped. "What could be so huge or whatever that would get you lost in thought?"

"By the request of a girl named Cristina, I walked her sister back to her house, getting her ice cream and a teddy bear and everything, to make sure she returned happy..." Chandler explained, looking at the ground again. "And you know what?"

The boy looked up again and smiled.

"I enjoyed it."


End file.
